Ethyl 6-Cyanoimidazo[1,2-a]pyridine-2-carboxylate → N-phenyl-6-cyanoimidazo[1,2-a]pyridine-2-carboxamide

HRID 2363723Notes

Reaction equation

HRID 2363723 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[N:10]=2)[CH:7]=1.[C:20](C1C=CC2N(C=C(C(OCC)=O)N=2)C=1)#[N:21]>>[C:14]1([NH:13][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([C:20]#[N:21])=[CH:7][N:6]3[CH:8]=2)=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 10512851Ethyl 6-Cyanoimidazo[1,2-a]pyridine-2-carboxylateHCID 247716736-bromo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Product 1

HCID 44135940N-phenyl-6-cyanoimidazo[1,2-a]pyridine-2-carboxamide

Procedure

By working in the same manner as for the preparation of Intermediate 1, replacing the ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate with ethyl 6-cyanoimidazo[1,2-a]pyridine-2-carboxylate (J. Med. Chem. (1998), 41(22), 4317), N-phenyl-6-cyanoimidazo[1,2-a]pyridine-2-carboxamide is obtained in the form of a yellow solid

Sources & evidence

ORD record
ord-fcce91f6a0394997a21fd452a65e36a7
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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